NP-MRD: Showing NP-Card for (2s,3r)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid (NP0329871)

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Record Information

Version

2.0

Created at

2022-09-12 14:41:25 UTC

Updated at

2022-09-12 14:41:25 UTC

NP-MRD ID

NP0329871

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid

Description

(2S,3R)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group. Based on a literature review very few articles have been published on (2S,3R)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    1.0525   -1.5147    0.9007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1968   -0.6419    0.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5048   -1.0409    0.7829 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5682   -0.2103    0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8562   -0.7023    0.7028 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3202    1.0649    0.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9903    1.4972   -0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8743    2.7859   -0.4877 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9203    0.6614    0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5620    1.0743    0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2433    2.2248   -0.3265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5543    0.2823    0.2996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8677    0.7130    0.1507 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6114    0.7875    1.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7349   -0.0386   -0.7946 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2418   -0.0583   -2.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145    0.5874   -0.8309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312   -1.4152   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1609   -2.3077   -0.1376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3387   -1.8244    0.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4823   -1.7895   -0.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4852   -2.5110    1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4253   -1.2176    1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6565   -2.0736    1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3115   -1.1530   -0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1495    1.7113   -0.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0686    3.2874   -0.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356    1.7810   -0.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5709   -0.1954    1.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6643    1.0106    1.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1884    1.6029    2.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1345   -0.0468   -2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6700   -0.9261   -2.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910    0.8890   -2.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6113    0.0826   -1.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8460   -2.3764   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  7  2  0
  7  8  1  0
  7  6  1  0
  6  4  2  0
  4  5  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  6
 15 18  1  0
 18 20  1  0
 18 19  2  0
  2  9  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 13 28  1  6
  8 27  1  0
  6 26  1  0
  5 25  1  0
  3 24  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 20 36  1  0
M  END


  Mrv1652309122216412D          

 20 20  0  0  1  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6039    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  1  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329871

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](OC(=O)C1=C(O)C=C(O)C=C1C)[C@](C)(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O7/c1-6-4-8(14)5-9(15)10(6)11(16)20-7(2)13(3,19)12(17)18/h4-5,7,14-15,19H,1-3H3,(H,17,18)/t7-,13+/m1/s1

> <INCHI_KEY>
QSVPEWAFDQHCIN-UHLUBPPHSA-N

> <FORMULA>
C13H16O7

> <MOLECULAR_WEIGHT>
284.264

> <EXACT_MASS>
284.089602855

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.0243087284287

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid

> <JCHEM_LOGP>
2.382192020666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.698435621394195

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.047725081931192

> <JCHEM_PKA_STRONGEST_BASIC>
-4.002913879133328

> <JCHEM_POLAR_SURFACE_AREA>
124.29

> <JCHEM_REFRACTIVITY>
68.3406

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.127   6.160   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.207   6.160   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R)-3-(2,4-Dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoate	Generator

Chemical Formula

C₁₃H₁₆O₇

Average Mass

284.2640 Da

Monoisotopic Mass

284.08960 Da

IUPAC Name

(2S,3R)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid

Traditional Name

(2S,3R)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](OC(=O)C1=C(O)C=C(O)C=C1C)[C@](C)(O)C(O)=O

InChI Identifier

InChI=1S/C13H16O7/c1-6-4-8(14)5-9(15)10(6)11(16)20-7(2)13(3,19)12(17)18/h4-5,7,14-15,19H,1-3H3,(H,17,18)/t7-,13+/m1/s1

InChI Key

QSVPEWAFDQHCIN-UHLUBPPHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

p-Hydroxybenzoic acid alkyl esters

Alternative Parents

Substituents

P-hydroxybenzoic acid alkyl ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Salicylic acid or derivatives
Benzoyl
Resorcinol
M-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Alpha-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Vinylogous acid
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.38	ChemAxon
pKa (Strongest Acidic)	3.05	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	68.34 m³·mol⁻¹	ChemAxon
Polarizability	27.02 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

183083

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid (NP0329871)

MOL for NP0329871 ((2s,3r)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid)

3D MOL for NP0329871 ((2s,3r)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid)

3D SDF for NP0329871 ((2s,3r)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid)

3D-SDF for NP0329871 ((2s,3r)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid)

PDB for NP0329871 ((2s,3r)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid)

3D PDB for NP0329871 ((2s,3r)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid)

SMILES for NP0329871 ((2s,3r)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid)

INCHI for NP0329871 ((2s,3r)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid)

Structure for NP0329871 ((2s,3r)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid)

3D Structure for NP0329871 ((2s,3r)-3-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-2-methylbutanoic acid)